Sodium hydride → HCID 178425256, compound

HRID 252982Notes

Reaction equation

HRID 252982 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH:5]=[N:6][NH:7][C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:11]=[C:10]([CH2:20][CH2:21]OS(C)(=O)=O)[N:9]=1.[N:30]1[CH:35]=[CH:34][C:33]([C:36]2[NH:37][C:38]([SH:41])=[N:39][N:40]=2)=[CH:32][CH:31]=1.[H-].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH:5]=[N:6][NH:7][C:8]1[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:11]=[C:10]([CH2:20][CH2:21][S:41][C:38]2[NH:37][C:36]([C:33]3[CH:34]=[CH:35][N:30]=[CH:31][CH:32]=3)=[N:40][N:39]=2)[N:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76837803methanesulfonic acid 2-{4-[N'-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethyl esterHCID 1785279605-pyridin-4-yl-1H-1,2,4-triazole-3-thiol

Product 1

HCID 178425256HCID 178425256, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 95, methanesulfonic acid 2-{4-[N′-(3-methyl-benzylidene)-hydrazino]-6-morpholin-4-yl-pyrimidin-2-yl}-ethyl ester (50 mg., 0.12 mmol) was dissolved in tetrahydrofuran (2 mL). To the reaction mixture was added 5-pyridin-4-yl-4H-[1,2,4]triazole-3-thiol (124 mg., 0.66 mmol) and sodium hydride (12 mg., 0.5 mmol) and the vessel was stirred at room temperature for sixteen hours. The solvent was removed under reduced pressure and the crude oil was purified by column chromatography to give Compound 25, N-(3-methyl-benzylidene)-N′-{6-morpholin-4-yl-2-[2-(5-pyridin-4-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-ethyl]-pyrimidin-4-yl}-hydrazine (34 mg.).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude oil was purified by column chromatography

Sources & evidence

ORD record
ord-bd8bb426d8a642d68913c686fa05ff47
Source dataset
uspto-grants-2011_01
Patent number
US07872005B2

Reaction notes

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